3-Aminonorharman, also known as 3-amino-β-carboline, is a tryptophan-derived β-carboline alkaloid found in various plant species. It is known to exhibit a range of biological activities, including anti-inflammatory, antidepressant, and anti-cancer properties. Synthesis of 3-aminonorharman often involves the Pictet-Spengler reaction of tryptamine and an appropriate aldehyde. Its effects are mediated through interactions with various receptors and enzymes, including serotonin receptors and monoamine oxidase. Research focuses on its potential therapeutic applications in conditions like depression, Alzheimer's disease, and cancer. Notably, 3-aminonorharman has been investigated for its ability to modulate neurotransmitter levels and inhibit the growth of certain cancer cells.'
3-aminonorharman: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 119537 |
| CHEMBL ID | 54381 |
| CHEMBL ID | 2171526 |
| SCHEMBL ID | 1982871 |
| MeSH ID | M0116447 |
| Synonym |
|---|
| 9h-pyrido(3,4-b)indol-3-amine |
| 9h-pyrido(3,4-b)indole, 3-amino- |
| 3-amino-9h-pyrido(3,4-b)indole |
| 3-aminonorharman |
| nsc-248005 |
| nsc248005 |
| CHEMBL54381 , |
| L002417 |
| 73834-77-2 |
| 9h-beta-carbolin-3-ylamine |
| bdbm50001472 |
| 9h-pyrido[3,4-b]indol-3-amine |
| CHEMBL2171526 |
| AKOS006228054 |
| 3-amino-beta-carboline |
| 3-amino-9h-pyrido[3,4-b]indole |
| SCHEMBL1982871 |
| DTXSID10224356 |
| UGMPOJSWOINMDE-UHFFFAOYSA-N |
| mfcd00209818 |
| 114819-72-6 |
| AMY213 |
| 3-amino-b-carboline |
| T71284 |
| 9h-i(2)-carbolin-3-ylamine |
| 2h-pyrido[3,4-b]indol-3(9h)-imine |
| WS-01320 |
| YCA83477 |
| aminonorharman, 3- |
| 89GRX55RRD |
| PD128565 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5057 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.4973 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.4988 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5046 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5065 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5057 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | IC50 (µMol) | 25.0000 | 0.0001 | 0.5075 | 10.0000 | AID40832; AID42344 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| plasma membrane | Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) |
| plasma membrane | Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) |
| plasma membrane | Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID701345 | Cytotoxicity against mouse Sarcoma 180 cells after 24 to 72 hrs by MTT assay | 2012 | Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10 | Structure-activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives. |
| AID40832 | In vitro inhibition of binding to the benzodiazepine receptor in rat cerebral cortical membrane using [3H]diazepam as radioligand | 1988 | Journal of medicinal chemistry, Sep, Volume: 31, Issue:9 | Synthesis of novel 3-substituted beta-carbolines as benzodiazepine receptor ligands: probing the benzodiazepine receptor pharmacophore. |
| AID42344 | In vitro binding affinity at benzodiazepine receptor of rat cerebral cortical membranes by [3H]diazepam displacement. | 1992 | Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22 | Predictive binding of beta-carboline inverse agonists and antagonists via the CoMFA/GOLPE approach. |
| AID701347 | Cytotoxicity against human HeLaS3 cells after 24 to 72 hrs by MTT assay | 2012 | Bioorganic & medicinal chemistry letters, May-15, Volume: 22, Issue:10 | Structure-activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives. |
| AID40825 | Inhibition of [3H]- flunitrazepam binding to GABA-A Benzodiazepine receptor of rat cerebral cortex membranes | 1985 | Journal of medicinal chemistry, Jun, Volume: 28, Issue:6 | 3-Amino-beta-carboline derivatives and the benzodiazepine receptor. Synthesis of a selective antagonist of the sedative action of diazepam. |
| AID493017 | Wombat Data for BeliefDocking | 1992 | Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22 | Predictive binding of beta-carboline inverse agonists and antagonists via the CoMFA/GOLPE approach. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 4 (66.67) | 18.7374 |
| 1990's | 1 (16.67) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 1 (16.67) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.21) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 6 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||